Effects on bioactivity due to C-5 heteroatom substituents on synthetic 28-homobrassinosteroid analogs

Five new 28-homobrassinosteroids have been synthesized, namely, (22R,23R)-5-fluoro-3α,22,23-trihydroxy-5α-stigmastan-6-one, (22R,23R)-5-fluoro-3β,22,23-trihydroxy-5α-stigmastan-6-one, (22R,23R)-5-fluoro-2α,3α,22,23-tetrahydroxy-5α-stigmastan-6-one, (22R,23R)-3α,5,22,23-tetrahydroxy-5α-stigmastan-6-o...

Descripción completa

Guardado en:
Detalles Bibliográficos
Autores principales: Ramírez, J.A., Gros, E.G., Galagovsky, L.R.
Formato: JOUR
Materias:
Bioactivity
Brassinosteroids
C-5 fluorinated analogs
C-5 hydroxylated analogs
brassinolide
brassinosteroid
phytohormone
article
chemical structure
hydrogen bond
molecular model
nonhuman
nuclear magnetic resonance
priority journal
reaction analysis
structure activity relation
structure analysis
synthesis
Acceso en línea:http://hdl.handle.net/20.500.12110/paper_00404020_v56_n34_p6171_Ramirez
Aporte de:
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
id todo:paper_00404020_v56_n34_p6171_Ramirez
record_format dspace
spelling todo:paper_00404020_v56_n34_p6171_Ramirez2023-10-03T14:50:39Z Effects on bioactivity due to C-5 heteroatom substituents on synthetic 28-homobrassinosteroid analogs Ramírez, J.A. Gros, E.G. Galagovsky, L.R. Bioactivity Brassinosteroids C-5 fluorinated analogs C-5 hydroxylated analogs brassinolide brassinosteroid phytohormone article chemical structure hydrogen bond molecular model nonhuman nuclear magnetic resonance priority journal reaction analysis structure activity relation structure analysis synthesis Five new 28-homobrassinosteroids have been synthesized, namely, (22R,23R)-5-fluoro-3α,22,23-trihydroxy-5α-stigmastan-6-one, (22R,23R)-5-fluoro-3β,22,23-trihydroxy-5α-stigmastan-6-one, (22R,23R)-5-fluoro-2α,3α,22,23-tetrahydroxy-5α-stigmastan-6-one, (22R,23R)-3α,5,22,23-tetrahydroxy-5α-stigmastan-6-one and (22R,23R)-3β,5,22,23-tetrahydroxy-5α-stigmastan-6-one. Their bioactivities were evaluated by the rice lamina inclination test. C-5α Fluorinated analogs showed excellent in vitro bioactivity, also revealed at low doses, while C-5α hydroxylated analogs resulted in an important decrease in bioactivity. Previously given explanations to justify the decreasing effect due to C-5α electronegative groups should be revised. (C) 2000 Elsevier Science Ltd. Fil:Ramírez, J.A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Gros, E.G. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_00404020_v56_n34_p6171_Ramirez
institution Universidad de Buenos Aires
institution_str I-28
repository_str R-134
collection Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic Bioactivity
Brassinosteroids
C-5 fluorinated analogs
C-5 hydroxylated analogs
brassinolide
brassinosteroid
phytohormone
article
chemical structure
hydrogen bond
molecular model
nonhuman
nuclear magnetic resonance
priority journal
reaction analysis
structure activity relation
structure analysis
synthesis
spellingShingle Bioactivity
Brassinosteroids
C-5 fluorinated analogs
C-5 hydroxylated analogs
brassinolide
brassinosteroid
phytohormone
article
chemical structure
hydrogen bond
molecular model
nonhuman
nuclear magnetic resonance
priority journal
reaction analysis
structure activity relation
structure analysis
synthesis
Ramírez, J.A.
Gros, E.G.
Galagovsky, L.R.
Effects on bioactivity due to C-5 heteroatom substituents on synthetic 28-homobrassinosteroid analogs
topic_facet Bioactivity
Brassinosteroids
C-5 fluorinated analogs
C-5 hydroxylated analogs
brassinolide
brassinosteroid
phytohormone
article
chemical structure
hydrogen bond
molecular model
nonhuman
nuclear magnetic resonance
priority journal
reaction analysis
structure activity relation
structure analysis
synthesis
description Five new 28-homobrassinosteroids have been synthesized, namely, (22R,23R)-5-fluoro-3α,22,23-trihydroxy-5α-stigmastan-6-one, (22R,23R)-5-fluoro-3β,22,23-trihydroxy-5α-stigmastan-6-one, (22R,23R)-5-fluoro-2α,3α,22,23-tetrahydroxy-5α-stigmastan-6-one, (22R,23R)-3α,5,22,23-tetrahydroxy-5α-stigmastan-6-one and (22R,23R)-3β,5,22,23-tetrahydroxy-5α-stigmastan-6-one. Their bioactivities were evaluated by the rice lamina inclination test. C-5α Fluorinated analogs showed excellent in vitro bioactivity, also revealed at low doses, while C-5α hydroxylated analogs resulted in an important decrease in bioactivity. Previously given explanations to justify the decreasing effect due to C-5α electronegative groups should be revised. (C) 2000 Elsevier Science Ltd.
format JOUR
author Ramírez, J.A.
Gros, E.G.
Galagovsky, L.R.
author_facet Ramírez, J.A.
Gros, E.G.
Galagovsky, L.R.
author_sort Ramírez, J.A.
title Effects on bioactivity due to C-5 heteroatom substituents on synthetic 28-homobrassinosteroid analogs
title_short Effects on bioactivity due to C-5 heteroatom substituents on synthetic 28-homobrassinosteroid analogs
title_full Effects on bioactivity due to C-5 heteroatom substituents on synthetic 28-homobrassinosteroid analogs
title_fullStr Effects on bioactivity due to C-5 heteroatom substituents on synthetic 28-homobrassinosteroid analogs
title_full_unstemmed Effects on bioactivity due to C-5 heteroatom substituents on synthetic 28-homobrassinosteroid analogs
title_sort effects on bioactivity due to c-5 heteroatom substituents on synthetic 28-homobrassinosteroid analogs
url http://hdl.handle.net/20.500.12110/paper_00404020_v56_n34_p6171_Ramirez
work_keys_str_mv AT ramirezja effectsonbioactivityduetoc5heteroatomsubstituentsonsynthetic28homobrassinosteroidanalogs
AT groseg effectsonbioactivityduetoc5heteroatomsubstituentsonsynthetic28homobrassinosteroidanalogs
AT galagovskylr effectsonbioactivityduetoc5heteroatomsubstituentsonsynthetic28homobrassinosteroidanalogs
_version_ 1782028043863195648

Ejemplares similares